


The Professor's Dilemma

by DeansDirtyLittleSecret



Series: Professor Dean Winchester AU [7]
Category: Supernatural
Genre: Alternate Universe - College/University, Angst, Explicit Language, F/M, Fluff, Professor Dean Winchester, Reader-Insert, not-canon
Language: English
Status: Completed
Published: 2015-08-02
Updated: 2015-08-02
Packaged: 2018-04-12 12:28:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,365
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4479275
Author URL: https://archiveofourown.org/users/DeansDirtyLittleSecret/pseuds/DeansDirtyLittleSecret
Summary: <blockquote class="userstuff">
              <p>Summary:  Professor Winchester wonders if he is really willing to do whatever he has to in order to protect his relationship with the reader.</p>
            </blockquote>





	The Professor's Dilemma

**Author's Note:**

> Dean's point of view

I watched Y/N run up the stairs, the muscles in her neck and back obviously tense and tight. I wanted to follow her, stop her before she got out the door, pull her into my arms and kiss her senseless. I wanted to remind her that I loved her, tell her I was sorry we were in this goddamn situation and I was going to do everything to fix it. But I didn’t. Instead I watched the woman I loved walk out the door, hurt and dejected. And there was nothing I could do about it.

I grabbed my coffee cup off the edge of my desk and went into my office, flipping the classroom lights off just before pushing the door closed. I wasn’t in the mood to talk to any students, so I was going to ignore the fact that I was supposed to have office hours right now. I refilled my cup from the pot on the low bookcase by the door, sloshing some more Jack Daniels into it. It was the only way I was going to make it through the rest of this day and the dinner date tonight.

I rubbed a hand over the back of my neck, wishing, not for the first time, that things had worked out differently. Wishing that Y/N wasn’t my student, or that I’d met her at a different time in my life or that Jo had never found out about us. All of this was my fault. If I hadn’t jumped into this so impulsively, if I’d just thought it through, made myself take a step back and really think before I’d rushed headlong into this relationship, then neither of us would be hurting. Of course, hindsight was 20/20 and I had a ton of it to spare.

I dropped to the couch - my ugly plaid couch - my feet up and my head resting on the armrest. I closed my eyes, but all I succeeded in doing was picturing the things that had happened on this couch between Y/N and I. God, I missed her, even though it had only been a couple of days since we’d been together. I was so screwed.

I remembered seeing her for the first time, standing in Sam’s living room at that party he’d begged me to attend. She’d been staring at me, blushing when I noticed her looking. When Sam had ditched me for his fiancee Cara and left me to fend for myself in a house full of drunken college students, I’d escaped outside to hide, only to run into Y/N. I’d struck up a conversation with her, pleasantly surprised at her quick wit and intelligence. I’d felt inexplicably drawn to her the second she’d opened her mouth and started to speak, a fact I’d made pretty clear when I’d kissed her after only knowing her for a couple of hours and then inviting her back to my place. Sam’s arrival had only delayed the inevitable.

I’d gone home that night only able to think about her, her number practically burning itself into my hand. I’d wanted to call her first thing Saturday morning, but I’d forced myself to wait, spending the weekend working in my classroom, trying not to think about her, something I hadn’t succeeded in doing.

Then the first day of school and my last class of the day had come around and there she was, sitting in the front row, corner seat, staring at me with those beautiful y/e/c eyes of hers, an unsure smile on her face. I knew then there was no turning back.

I didn’t regret anything that had happened between Y/N and I, and I never would. I certainly didn’t regret falling in love with her. I didn’t care what it took, I was going to make this work. I wasn’t about to let the best thing that had ever happened to me slip away.

My only regret was not being more cautious. I should have known that Jo would try something; she’d made it perfectly clear that she was interested in me that first night at the bar and she hadn’t wanted to take no for an answer. She’d been furious when I’d rejected her after she’d peeled off her clothes and tried to kiss me in my classroom. She’d put her clothes back into place, embarrassed and angry that I had refused her, informing me that I was making a mistake. Her anger had only been fueled by my refusal to return her calls or text messages. I hadn’t told Y/N about the constant barrage of messages and calls I had actually been receiving from Jo, choosing instead to keep it to myself. I’d incorrectly assumed that Jo would grow tired of whatever game it was she was playing and she’d move onto some other poor guy. I couldn’t have been more wrong.  

My cell phone vibrating in my pocket pulled me out of my musings. I yanked it free, hoping it was Y/N, even just a text message. I was craving any kind of contact with her.

It was a text, but it was from Sam, with the details of our double date. I acknowledged it, told him I’d see him at the restaurant later that night. He sent me another text, asking me if I wanted to pick up Jo at his place. I immediately answered no and told him I would meet them at the restaurant. I wasn’t going to give an inch. Jo might think she had me right where she wanted me, but she was wrong. I wasn’t a man that should be underestimated.

* * *

I stayed in my office as long as I possibly could, trying to lose myself in my work. I wasn’t having much luck, I kept distracting myself with memories of the first time Y/N and I had kissed on my ugly plaid couch or the first time we’d had sex on that same couch. I considered going home, but that was no better, there wasn’t a room of that house that didn’t remind me of her or something we’d done.

When it got to a point where I absolutely could not postpone leaving any longer, I grabbed the keys to the Impala and made my way the short distance across campus to the staff parking lot. I slid into my car, one of the few places I felt like I belonged. It had been my father’s car, one of the only constants in my life after my mother had passed away when I was four. Dad had moved us around a lot, never staying in one place for long. I’d grown up all over the country, experiencing life in a way other children didn’t. When my dad had died the year after I graduated college, the only thing I’d kept was his car. The hardest thing about teaching overseas had been leaving her behind.

The restaurant where I was having dinner with Sam, Cara and Jo was on the other side of town, giving me time to think some more about the situation Y/N and I were now in. I needed to get a hold of Jo’s phone, get rid of those pictures. Of course, the only way I would be able to do that would be to get close to her and I had no intention of doing that. And there was no guarantee that she hadn’t saved the photos elsewhere. I’d just have to figure it out as I went along. One thing I knew for sure, Jo wasn’t going to get one moment of enjoyment out of this evening.

Sam was waiting for me just inside the restaurant when I walked in. “Dude, I was starting to think you weren’t coming,” he laughed.

I rolled my eyes, forcing myself to smile at my long time friend. “Nah, just got caught up at work,” I said. “Let’s get this over with.”

“You’re really not on board with this idea are you?” Sam asked as I followed him through the restaurant. “I know she’s my sister -”

“It’s not because she’s your sister,” I interrupted, stopping him with a hand to his arm. “Let’s get something clear. I’m not interested in dating Jo, Sam. No offense or anything, but she’s not exactly my type.”

“I know she comes on a little strong,” Sam said. “But she’s not that bad once you get to know her a little better.”

“I’m not that interested in getting to know her better,” I explained. “Look, I agreed to this because you asked me, let’s just get through the evening, okay?”

Sam nodded glumly, gesturing for me to follow him. Our table was in the back corner of the restaurant. Cara and Jo were sitting across from each other, watching us as we made our way across the room. A smug smile spread across Jo’s face; she looked like the proverbial cat that swallowed the canary. If she thought my presence here indicated an acceptance of the situation, she was definitely in for a surprise.

Sam, predictably, sat in the chair next to Cara, leaving me to sit in the unoccupied seat by Jo. As soon as I sat down, she slid her hand onto my thigh, squeezing it gently and smiling at me. Having already made the mistake of letting her get too touchy once before, I quickly took hold of it and set it back on her leg. I didn’t even try to keep the grimace off of my face.

I didn’t miss the confused glance Cara shot Sam’s way, or his obvious discomfort, though neither of them said anything about it. Jo, on the other hand, wasn’t able to keep the pissed, insolent look off of her face. She sipped her water, watching me out of the corner of her eye.

Cara cleared her throat, tossing another look at Sam. “Um, so, Dean,” she said. “Sam tells me you’re settling in pretty well. Are you enjoying the university? It must be so much different from Rome.”

“I do miss living in Italy. Especially the food,” I replied. “But I’m glad to be back in the States.”

“He missed his car,” Sam chuckled.

“Damn right I missed my car,” I added.

“His car is gorgeous,” Jo purred. “I can’t wait to go for a ride in it.” I glance over at her, only to see her eyebrows raise suggestively and one corner of her mouth pulled up in a smirk.

“Yeah, that’s not going to happen,” I muttered under my breath, though I made sure I said it loud enough for Jo to hear.

Cara’s eyes widened slightly, so I must not have been as quiet about it as I thought. She glanced again at Sam, then, apparently determined to try and make conversation, she turned back to me and forced a smile onto her face.

“So, no Italian girl managed to sweep you off of your feet?” she asked. “I mean, I have to assume since you’re here you don’t have a girlfriend…?” She left the question hanging in the air.

“Not exactly,” I replied. “There is a girl -”

“But they’re not together anymore,” Jo interjected. “Right, Dean?”

Instead of answering, I signalled the waitress and ordered a drink, the first of many.

Dinner was worse than I’d imagined, extremely awkward and uncomfortable. I felt like a surly teenager all evening, disagreeable and argumentative. I barely kept up my side of the conversation, grunting answers and slamming back drink after drink, though the alcohol didn’t seem to have any affect on me. I was actually starting to feel bad for Sam and Cara who were desperately trying to salvage the evening, Cara in particular. She kept asking questions, trying to draw me out, but I was steadfast in my resolve to make this evening as miserable as possible for Jo.

It seemed to be working. By the time dessert was brought to the table, Jo was no longer smiling and she was downing her fair share of alcohol as well. Cara had given up trying to draw me into conversation and Sam was glaring at me with a bitchface to end all bitchfaces. I felt like a complete ass.

I excused myself to go to the restroom; I needed a break from the tension at the table. I splashed some cold water on my face and stared at myself in the mirror. I was pretty sure I was effectively destroying my friendship with Sam; I’d be lucky if he ever talked to me after this night.

I wasn’t really surprised to see that Sam and Cara were no longer at the table when I came out of the bathroom. Jo was sitting alone, a glass of wine in her hand, staring at the wall. I took the seat most recently occupied by her brother.

“Sam and Cara took off?” I asked.

“Yeah, I think they’d had enough of you being an asshole,” she snapped. “I’m surprised you even bothered to come back. Seems like you had the perfect chance to escape.”

“I wanted to make sure the bill was paid,” I said, shrugging.

“Sam took care of it,” Jo muttered.

“I don’t know what you thought was going to happen tonight,” I sighed. “Did you think I was going to be all smiles and happy about being forced to go on a date with you? That I’d be okay with you threatening my career, my livelihood, so you could get what you wanted?”

We stared at each other across the table, neither of us willing to give in. Jo finally looked away, but only long enough to pull her phone from her purse. She did something with it, keeping it close against her body the entire time. A few seconds later my phone vibrated. I pulled it from my pocket. Jo had sent me one of the pictures - me, with head between Y/N’s legs, a look of pure bliss on her face.

“You shouldn’t be fucking your teaching assistant,” Jo said. “Is that what it takes to get an A in your class, Professor?”

“You don’t know anything, you know that, don’t you?” I growled. “You think you’ve got this all figured out, but you don’t have a clue. You can’t see anything but the fact that Y/N has something you want.”

Jo shook her head, her blonde hair flying around her face. “No, I see someone who’s breaking the rules and doesn’t want to get caught. That’s why you’re here, isn’t it? Forget all of your bullshit, what this all boils down to is you doing whatever you can to save your own ass.” She smiled. “You don’t care anymore about Y/N than I do. If you did, you’d march into the university president’s office and tell him the truth, consequences be damned. So you can sit over there and lecture me all you want, Professor, but we all know that you’re only using her for sex.” She stood up, swallowed the rest of her drink and set her glass down on the table. “I’m just offering you an alternative.” She pulled her jacket off the back of the chair and swung her purse over her shoulder. “You have my number, call me when you decide what you want to do.”

I watched her walk out of the restaurant, wondering how one person could be that self-absorbed and that selfish. But she had a point. I kept telling myself I was willing to do anything to make my relationship with Y/N work, but was I really? How far was I willing to go to make it work?

* * *

I popped a couple of aspirin, downing them with the huge cup of coffee I’d picked up in the student union. I rubbed the spot on my forehead just above my eyes, praying I could hold the headache off by sheer will alone. I shouldn’t have had so many drinks the night before, I was regretting it this morning. I sat in my office with the light off, staring at the phone on my desk, wondering how long it would be before the university president’s secretary got back to me about the appointment I’d requested.

I wasn’t sure how long I sat in the dark, but it was long enough for my headache to fade slightly. I could feel myself nodding off, the hangover and nearly sleepless night beginning to affect me, until I heard the door of my classroom open and close and the lights came on. I could hear Y/N’s familiar gait as she walked down the stairs and dropped her bag to the floor beside the desk. I pushed myself off of the couch and sauntered to the door. I watched her for a few minutes as she pulled her things from her backpack, her pen in her mouth, her brow furrowed in concentration. She looked exhausted, like she hadn’t slept at all. I knew that was my doing.

“Hey,” I said.

She jumped and shot me a dirty look. “You scared the shit out of me! What are you doing? Hiding in the dark?”

“Sort of,” I chuckled. “Headache. What are you doing here so early?”

“My first class was canceled,” she snapped. She looked me up and down, most likely noting my exhaustion. “Date too much for you last night?”

“Nothing happened, Y/N, I promise you. I should have called you when I got home,” I tried to explain. “But I had a lot to drink and I fell asleep. I...Those are just excuses, I should have called. I’m sorry.”

“You don’t owe me anything,” she mumbled, shaking her head. “It’s okay.” She turned her back on me, that same tension I’d noticed yesterday in her neck and shoulders.

I couldn’t take it anymore. I hadn’t touched her in days, I ached to kiss her, to hold her in my arms. I took two steps out of my office, grabbed her hand and pulled her into the office with me, kicking the door closed with my foot.

“Dean, we can’t,” she protested halfheartedly.

“I don’t care, Y/N,” I moaned, pulling her into my arms. I caught her lips in a slow, tender kiss, rubbing my hand up and down her back, holding her close to me. She wrapped her arms around my waist and relaxed against me, letting me support her. I could have stayed there with her all day, hiding from the rest of the world. I ran my hands over her body, the feel of her in my arms was almost therapeutic. I held her close to me, wanting her body against mine, her breath mingling with mine. I wanted to touch her, caress her, kiss every inch of her skin. I was tempted to do it, screw the worry and the fear of being caught. I needed her.

“Dean!” a voice called loudly from the other side of the door.

Startled, Y/N took a step away from me. “Who’s that?” she whispered.

“Hey Dean, you here?” the voice repeated, then there was a sharp knock on my office door.

“It’s Sam,” I said. “Stay here.” I gave her a stern look, then opened my office door just enough so I could slip out. I left it slightly ajar, I didn’t want her to think I was hiding anything from her.

“There you are,” Sam said. He took a couple of steps back, his arms crossed over his chest, his hazel eyes flashing in anger. I recognized the stance immediately, I’d seen it dozens of times during our college years. It usually meant someone was about to get their ass kicked. I had a feeling that it was me.

“What are you doing here, Sam?” I asked, though I was pretty sure I knew.

“What the fuck was that last night, Dean?” he shouted. “You were an utter and complete asshole. I’ve never seen you act like that. I know you didn’t want to be there, but you didn’t have to be a fucking jerk.”

“Sam…” I started.

“Seriously Dean, that was so unlike you,” he interjected. “Cara thinks you’re a ass and after last night, I might have to agree. I spent two hours trying to convince her you were sick or something, but I don’t think she bought it. She might think you’re an alcoholic though, after the way you were drinking. I don’t know what the hell your goddamn problem is, but you need to get over it.”

“Just let me explain,” I said.

“Explain?” Sam grumbled. “I don’t think anything can explain that. I used to think you were a good guy, my best friend, but after that, I don’t even know anymore. And my sister, holy shit but you were a dick to her. She didn’t deserve that…”

“Wait a minute,” I snapped. “Your sister was the reason I was acting like that!”

“What?” Sam huffed. “Don’t blame being an asshole on my sister.”

I took a deep breath. This might potentially be a huge mistake, but I could not let it continue. This crap with Jo was snowballing out of control and I needed to do something. Not only was she threatening my career and my relationship with Y/N, but now my friendship with Sam was in jeopardy. “Your sister managed to get some pictures of me in a, let’s say, compromising position and she is now using them to try to get me to date her. Or at least sleep with her.”

“My sister is blackmailing you?” Sam asked, shock written all over his face. “Bullshit.”

“You’re my friend, right Sam?” I asked. “I can trust you?”

Sam ran his fingers through his shaggy hair. “I guess, yeah,” he said. “Just explain to me what the hell is going on.”

I explained what had happened - meeting a student, falling for her, everything, right down to the sex in the library and his sister getting pictures of it. The only thing I didn’t tell him was who the student was.

“I don’t know Dean. That’s really shitty and...well, she’s my sister. How am I supposed to believe that she could do something like that?” Sam muttered.

“I know it sounds crazy,” I replied. “But it’s the truth. All of it.”

“I don’t know, Dean,” Sam repeated. It was clear he wasn’t sure whether or not he should believe me.

I heard a creaking sound as my office door opened all the way and then Y/N clearing her throat. She had her hands clenched so tightly in front her that her knuckles were white.  “It’s true, Sam.” She looked over at me and shrugged, mouthing an apology.

“Y/N?” Sam said. “Wait, are you...are you the student?”

“Yes, I am,” Y/N said stepping from my office. “And I swear to God, everything Dean said is true. Look, I know Jo’s your sister, but it’s the god’s honest truth. She took those pictures of us and she’s using them to force Dean to...I don’t know, do whatever she wants him to do, I guess.”

“But, you’re...you’re Jo’s friend,” Sam muttered. “Why the hell -” He stopped, swallowing loudly. “Why would she do this?” He paced in circles in front of my desk, raking his hands through his hair, then he yanked his phone from his pocket and before either Y/N or I could protest, he had dialed.

“Jo,” he barked into the phone. “Where are you?”

I watched his face as he spoke to his sister, demanding she meet him in my classroom. She must have argued with him, because he turned his back, but I could hear the anger in his lowered voice, the older brother, don’t-give-me-any-shit tone that insisted she meet him _now_ , whether she liked it or not. Once he disconnected the call, he turned to me.

“She’s on her way here,” he said. “We’ll talk this out. Why don’t we wait in your office?”

I agreed, pushing open the door and gesturing for everyone to go inside. I gave Y/N’s hand a quick squeeze when she walked past me to sit on the couch. She closed her eyes and rested her head against the back. Sam returned to pacing, not speaking, his face hard and angry. I sat behind the desk, my eyes on Y/N. I didn’t like how drawn and tired she looked.

The silence in the room was thick, like congealing blood. I tried to think of something to say to break the tension, but I couldn’t come up with anything. Instead, I drummed my fingers on the table and stared at Y/N, worrying about her.

As soon as Sam heard the door to my classroom open, he whipped open the office door, stalking out of the room with a determination I had never seen before. A few seconds later he was back, his hand around Jo’s elbow, firmly guiding her into the office. They stopped in front of my desk, though he didn’t release her.

“What the hell is this?” she grumbled, looking in turn at each of us. “Some kind of intervention?” She snorted.

“Give me your phone, Jo,” Sam demanded.

“What?” she whispered. She turned to stare at him, her hand involuntarily tightening on the strap of her purse.

“I want your phone, Jo,” Sam said. “Now.”

“I’m not giving you my phone,” she said.

“Give it to me or I take it,” he ordered. He pulled himself to his full height, a full foot taller than his petite sister. He glowered down at her, waiting.

Jo stared at him for almost a full minute, then she let out a huffy breath, opened her purse and handed her phone to her brother. He swiped a finger across it, then held it out to her.

“Unlock it,” he said.

She reached out, punched several numbers into the phone, then nodded weakly. Sam held the phone in his hand, his fingers flying over the screen. I knew the second he found the pictures, because his eyes widened noticeably and he momentarily stopped breathing. He looked up slowly, his hazel eyes meeting his sister’s brown ones. He looked at both Y/N and I, then back at the phone.

“Jesus Christ, it’s true,” he sighed heavily. “You really did this.” He turned the phone around, the picture of me straightening Y/N’s clothes on the phone. He thrust it into her face. “What the fuck were you thinking?”

She shot a nasty look my direction, as if I was responsible for what she had chosen to do. She tried to snatch the phone away from him, but he yanked it out of her reach, then shoved it into his pocket.

“Where else do you have these saved?” he asked calmly.

Jo shot a glare so deadly at her brother that I was surprised he didn’t keel over. “I don’t want to talk about this right now,” she snapped.

“Why the hell would you do this?” Sam asked. “Y/N is your friend and Dean is mine. How could you do something like this?” He waited for her to answer, but when she didn’t, he took a deep breath. “I’m asking you nicely, Joanna Beth, where else do you have these saved?”

“I said I don’t want to talk about this.” Jo crossed her arms like a petulant child, her eyes darting around the room, never quite landing on any of us. She pressed her lips together, refusing to say another word.

Before I realized what was happening, Y/N was off the couch and across the room, slapping Jo so hard across the face that her head whipped almost completely around. A bright red handprint immediately appeared on her cheek.

“You bitch,” she spat, her hand covering the mark on her face.

“I’m the bitch?” Y/N snapped, her hand coming back to hit Jo again. I lunged around the desk, grabbed Y/N and pulled her away from Jo. Sam took a hold of his sister, restraining her before she retaliated.

Sam looked like he had swallowed a bug. He ran a hand through his shaggy hair and turned to me. “I’m sorry, Dean. I promise you I will take care of this.” He took hold of Jo’s elbow and led her out of the room.

I could hear him talking as they left the room, his voice harsh and angry, though I couldn’t quite make out what he was saying. When I heard the classroom door close, I turned to Y/N.

“You okay?” I asked.

She nodded, supporting herself on my desk with one hand. She glanced out the still open door and sighed loudly; it was only a few minutes until my first class started. “Do you really think Sam will take care of it?” she murmured.

“I know he’s going to try,” I replied. “If not, then I…”

“Professor Winchester!” My classroom door flew open and Adam, one of my more needy freshman students, came barreling down the stairs, so fast I thought he might fall headfirst to the bottom. “Professor Winchester, I need to talk to you!” He spotted me immediately, rushing across the room and into my office with no invitation. “I’m having some issues with my paper. Can I ask you a few questions?” He glanced at Y/N, giving her a small wave.

Y/N gave me a frustrated smile, grabbed a couple of books off of my desk, and excused herself. I watched her through the door as she set to work preparing for my first class, barely hearing anything Adam was saying.

“Professor?” Adam said.

“Sorry, what were you saying?” I forced myself to focus my attention on Adam and his questions.

By the time I was able to shoo Adam out of my office, Y/N had already started teaching the class. I left the office door open and settled myself at my desk, trying to concentrate on the outline I was working on, but instead checking my phone every few minutes for any kind of communication from Sam. Class was over, students leaving, before I finally received the message I’d been hoping for.

“Pictures gone. All of them. Sorry about all of this. I’d like to say Jo is sorry, but I don’t think she is. She’s fucked in the head. Let’s get a beer later this week.”

I shot back a quick thank you, agreeing to meet for beers later. I pushed myself away from my desk, yelling for Y/N, forgetting for a few seconds that there would still be students wandering in and out of the room. She appeared in the doorway a second later, a confused yet hopeful look on her face.

I waited as the last stragglers left, watching the door for anyone to come, fully aware that my next class started in a few minutes. I reached out, the tips of my fingers just resting on her hip. I was filled with that overwhelming need to touch her again, but this would have to be enough. For now.

“Sam took care of it,” I said. “The pictures are gone.”

“Really?” she whispered. I could see the tension drain out of her. She glanced over her shoulder, then raised up on her toes and quickly pressed a kiss to my lips. “Thank God.”

The phone on my desk interrupted any further discussion. I kissed her one more time. “My house, tonight,” I murmured. “We’ll celebrate.”

She nodded her agreement, pulling the door closed behind her. I hurried back to my desk.

“Hello?” I answered the phone.

“Professor Winchester?” the female voice on the other end asked. “This is Mr. Shurley’s assistant. He’d like to meet with you at four p.m. today. Would that be a good time for you?”

I readily agreed, figuring I would just have to cancel my afternoon class. A meeting with the university president was too important to miss, especially when I had been the one to request it.

One way or another, everything would be settled by tonight.


End file.
